34683-73-3

Usage

Uses

1-Chloro-6-iodohexane is used as :Pharmaceutical intermediates.

General Description

1-Chloro-6-iodohexane is an α,ω-dihaloalkane. 1,12-dichlorododecane is formed as a major product from the reduction of 1-chloro-6-iodohexane with nickel(I) salen. It affords 8-chloro-1-octyne on coupling with sodium acetylide.

InChI:InChI=1/C6H5ClIN/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2

Upstream product

• 629-11-8 1,6-hexanediol 
• 401564-36-1 (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 618-27-9 hydroxy L-proline 
• 591-50-4 iodobenzene 
• 41327-15-5 5-bromo-3-methyl-1-phenyl-1H-pyrazole 
• 100-63-0 phenylhydrazine 
• 947-95-5 5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole 
• 19735-89-8 3-methyl-1-phenylpyrazolin-5(4H)-one 
• 401566-79-8 1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine 
• 906093-30-9 1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine acetate 
• 88050-17-3 N-Fmoc-trans-4-Hydroxy-L-Proline 
• 33996-33-7 oxaceprol 

Downstream Products

• 24088-97-9 8-chloro-oct-1-yne 
• 56554-74-6 1-chloro-7-heptadecyne 
• 331651-05-9 3-(6-chlorohexyloxy)-3',4'-dibenzyloxyflavone 
• 7432-41-9 8(Z)-heptadecenoic acid 
• 1209005-66-2 C₁₈H₂₈Cl₂O₂ 
• 1207202-29-6 2-(6-chloro-hexyl)-3-fluoro-benzoic acid ethyl ester 
• 1395081-85-2 C₄₁H₃₇ClO 
• 1395081-89-6 1-(1-(5-pyridiniumhexyloxy)-2,3,4,5-tetraphenylcyclopenta-2,4-dienyl)benzene chloride 
• 1609476-56-3 1-(4-((24-chloro-3,6,9,12,15,18-hexaoxatetracosyl)oxy)-5-methoxy-2-nitrophenyl)ethanone 
• 1609476-57-4 1-(4-((24-chloro-3,6,9,12,15,18-hexaoxatetracosyl)oxy)-5-methoxy-2-nitrophenyl)ethanol 
• 1609476-58-5 1-(4-((24-chloro-3,6,9,12,15,18-hexaoxatetracosyl)oxy)-5-methoxy-2-nitrophenyl)ethyl (4-(((2-amino-9H-purin-6-yl)oxy)methyl)benzyl)carbamate 
• 544-10-5 1-Chlorohexane 
• 928-89-2 6-chlorohexene 
• 3922-28-9 1,12-dichlorododecane 

Relevant academic research and scientific papers

Manganese-Mediated Direct Functionalization of Hantzsch Esters with Alkyl Iodides via an Aromatization-Dearomatization Strategy

We report, for the first time, manganese-mediated direct functionalization of the Hantzsch esters with readily accessible alkyl iodides through an aromatization-dearomatization strategy. Applying this protocol, a library of valuable 4-alkyl-1,4-dihydropyridines were facilely afforded in good yields. This simple and practical reaction proceeds under visible-light irradiation at room temperature and displays high functional-group compatibility. Additionally, the method is applicable for gram-scale synthesis and late-stage functionalization of complex molecules.

Quinim: A New Ligand Scaffold Enables Nickel-Catalyzed Enantioselective Synthesis of α-Alkylated ?-Lactam

Herein, we report a nickel-catalyzed reductive cross-coupling reaction of easily accessible 3-butenyl carbamoyl chloride with primary alkyl iodide to access the chiral α-alkylated pyrrolidinone with broad substrate scope and high enantiomeric excess. The current art of synthesis still remains challenging on the enantioselective α-monoalkylation of pyrrolidinones. The newly designed chiral 8-quinoline imidazoline ligand (Quinim) is crucial for maintaining the reactivity and enantioselectivity to ensure the reductive cyclization of monosubstituted alkenes for unprecedented synthesis of chiral non-aromatic heterocycles.

Preparation method of 1-chloro-6-iodohexane

The invention discloses a preparation method of 1-chloro-6-iodohexane. The preparation method comprises the steps of with 6-chloro-1-hexanol and p-toluene sulfochloride as the materials and benzene ortoluene as a solvent, reacting at (-5)-(5) DEG C for 2-5 hours under the effects of a phase transfer catalyst and an acid-binding agent so as to prepare 4-methylbenzenesulfonic acid-6-chlorohexyl ester, and carrying out reflux reaction on 4-methylbenzenesulfonic acid-6-chlorohexyl ester and sodium iodide for 0.5-3 hours, so as to prepare 1-chloro-6-iodohexane. The preparation method has the characteristics of easiness in operation, simplicity and convenience in after-treatment and relatively high yield.

OXALATE SALTS OF TENELIGLIPTIN AND SOLVATES THEREOF, INTERMEDIATES, PROCESS OF PREPARATION

The present invention provides oxalate salts of teneligliptin and solvates thereof exhibiting superior physiochemical properties. In particular, crystalline form of teneligliptin 2.5 oxalate 1.0 hydrate and crystalline form of teneligliptin 3.0 oxalate 1.0 hydrate are disclosed. Also provided are methods of preparing the same, and uses thereof.

Method for preparing hydrobromic acid teneligliptin

The invention provides a method for preparing hydrobromic acid teneligliptin. The method includes steps of preparing L-hydroxyproline; mixing the L-hydroxyproline and sodium bicarbonate with each other to obtain mixtures, dissolving the mixtures in water, adding acetone into the water, dropping di-tert-butyl dicarbonate into the water, carrying out room-temperature reaction overnight and then treating reaction products to obtain t-butyloxycarboryl-N-hydroxyproline; preparing t-butyloxycarboryl-N-4-oxo-proline from the t-butyloxycarboryl-N-hydroxyproline; preparing (2S)-4-oxo-2-(3-thiazolidine carbonyl)-1-pyrrolidine carboxylic acid tert-butyl ester from the t-butyloxycarboryl-N-4-oxo-proline; preparing compounds III from compounds IV; preparing compounds II from the compounds III; preparing compounds 1-(3-methyl-1-phenyl-1H-pyrazole-5-base) piperazine from the compounds II; preparing intermediates I; preparing the hydrobromic acid teneligliptin from the intermediates I. The method has the advantages that the method is low in cost, and the cost of the method is only two-thirds of the cost of an existing method in the prior art; the yield of the hydrobromic acid teneligliptin is higher than 95%, and the purity of the hydrobromic acid teneligliptin is higher than 98%.

Process for the preparation of teneligliptin

A process for the preparation of teneligliptin.

Discovery and preclinical profile of teneligliptin (3-[(2S,4S)-4-[4-(3- methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl] thiazolidine): A highly potent, selective, long-lasting and orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

Dipeptidyl peptidase IV (DPP-4) inhibition is suitable mechanism for once daily oral dosing regimen because of its low risk of hypoglycemia. We explored linked bicyclic heteroarylpiperazines substituted at the γ-position of the proline structure in the course of the investigation of l-prolylthiazolidines. The efforts led to the discovery of a highly potent, selective, long-lasting and orally active DPP-4 inhibitor, 3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5- yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine (8g), which has a unique structure characterized by five consecutive rings. An X-ray co-crystal structure of 8g in DPP-4 demonstrated that the key interaction between the phenyl ring on the pyrazole and the S2 extensive subsite of DPP-4 not only boosted potency, but also increased selectivity. Compound 8g, at 0.03 mg/kg or higher doses, significantly inhibited the increase of plasma glucose levels after an oral glucose load in Zucker fatty rats. Compound 8g (teneligliptin) has been approved for the treatment of type 2 diabetes in Japan.

Pheromone synthesis. Part 244: Synthesis of the racemate and enantiomers of (11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), a new sex pheromone of male Drosophila melanogaster to show its (S)-isomer and racemate as bioactive

The enantiomers of (11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol were synthesized from the enantiomers of 3,4-epoxy-1-butanol PMB ether. Its racemate was also synthesized. Its (S)-isomer and racemate were shown to possess the same pheromone activity as CH503, a long-lived inhibitor of male courtship in Drosophila melanogaster, although the racemate was less active.

CONCOMITANT PHARMACEUTICAL AGENTS AND USE THEREOF

A concomitant agent to be used simultaneously or separately, comprising a combination of (a) 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine, a salt of the compound with an organic or inorganic and mono- or di-basic acid or a solvate thereof, and (b) at least one kind of active ingredient selected from the group consisting of an active ingredient of a pharmaceutical agent selected from (i) an antidiabetic drug, (ii) a lipid lowering drug, (iii) an antihypertensive drug, (iv) a therapeutic drug for diabetic complications, (v) an antiobesity drug, (vi) an antiplatelet drug and (vii) an anticoagulant, a pharmaceutically acceptable salt thereof and a solvate thereof.

SALT OF PROLINE DERIVATIVE, SOLVATE THEREOF, AND PRODUCTION METHOD THEREOF

The present invention provides 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine (compound I) useful as a dipeptidyl peptidase-IV inhibitor, which has superior properties of stability and hygroscopicity, and reproducible crystal structure, and a production method thereof.